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Synthesis and Properties of 1,2-Bis(5,5′-dinitramino-1,3,4-oxadiazol-2-)ethane
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Science and Technology on Aerospace Chemical Power Laboratory, Hubei Institute of Aerospace Chemotechnology, Xiangyang 441003, China

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    Abstract:

    In order to obtain insensitive 1,3,4-oxadiazole energetic compounds, 1,2-bis(5,5′-dinitramino-1,3,4-oxadiazol-2-)ethane(BNOE) was synthesized via hydrazinolysis, cyclization and nitration using dimethyl succinate and cyanogen bromide as raw materials with a total yield of 49.93%. Its structure was characterized by elemental analysis, FT-IR and NMR. The thermal decomposition process was studied by TG-DSC, and the mechanical sensitivities were tested according to the GJB5891-2006 method. The density was measured using the density bottle method. The solid-state heat of formation (HOF) was calculated with Gaussian 09 software. The detonation parameters were calculated with EXPLO 5 v6.02 software. Results show that the onset decomposition temperature of BNOE is 202.2 ℃ and thermal decomposition peak temperature is 208.6 ℃. The sensitivity towards impact, friction, and electrostatic of BNOE is 8.6 J, 88%, and 108.1 mJ, respectively. The measured density is 1.714 g·cm-3, the solid heat of formation is 48.25 kJ·mol-1. The calculated detonation velocity and pressure is 7663 m·s-1 and 22.6 GPa, respectively. The study on cyclization mechanism of 5-methyl-2-amino-1,3,4-oxadiazole (NAOz) by Gaussian 09 show that the reaction proceeds in two stages: hydrazinolysis and ring formation.

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马英杰,卢艳华,曹一林,等.1,2-双(5,5′-二硝胺基-1,3,4-噁二唑-2-)乙烷的合成与性能[J].含能材料,2020,28(7):678-684.
MA Ying-jie, LU Yan-hua, CAO Yi-lin, et al. Synthesis and Properties of 1,2-Bis(5,5′-dinitramino-1,3,4-oxadiazol-2-)ethane[J]. Chinese Journal of Energetic Materials,2020,28(7):678-684.

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History
  • Received:December 22,2019
  • Revised:May 07,2020
  • Adopted:April 13,2020
  • Online: April 27,2020
  • Published: July 25,2020